Chemical synthesis methodologies research from the laboratory of Assistant Professor of Chemistry Max Majireck was recently published online in the journal Tetrahedron Letters.
Five student and alumni co-authors contributed to this project over the course of summer research and senior projects from 2014 to 2016: John Bennett ’16, Jonathan Shapiro ’17, Tina Choinski ’15, Yingbin Mei ’16 and Sky Aulita ’15.
The article, “Synthesis of phthalan and phenethylamine derivatives via addition of alcohols to rhodium(II)-azavinyl carbenoids,” describes new chemical reactions developed by the Majireck lab to quickly access a class of bioactive molecules known as phenethylamines and phthalans.
The group made use of a recently developed rhodium-catalyzed reaction to access a highly reactive chemical species that combines with various alcohols to generate products with unique molecular structures.
The researchers also explored the chemical behavior of an unusual group of atoms, known as an N-(2-alkoxyvinyl)sulfonamide, found within their products. This structure, defined as a “functional group” due to its effect on the molecules’ reactivity, enabled the lab to identify other novel reactions that can be used in the synthesis of nitrogen and oxygen-containing compounds with potentially useful biological activity.
Biological testing of multiple compounds produced from this research is underway. The group hopes to identify new molecules that can be used by other labs to study fundamental processes in disease biology.